


Working Nights

by Lil_Jei



Category: The Alienist (TV), The Alienist - Caleb Carr
Genre: Crossdressing, M/M, Prostitution
Language: English
Status: Completed
Published: 2018-08-22
Updated: 2018-08-31
Packaged: 2019-07-01 06:29:17
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,956
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15768501
Author URL: https://archiveofourown.org/users/Lil_Jei/pseuds/Lil_Jei
Summary: Title: Working NightsAuthor:Like JeiFandom: The AlienistPairing: John Moore/ Theodore RooseveltRating: PG 13Word Count: UNKDisclaimer: Not mine, no $ madeA/N: Plot bunny, drabble, WIP, un-beta'd.Summary: John finds himself working undercover in a brothel.





	1. Chapter 1

John couldn't believe the depths to which he'd sunk to. Despite being wealthy to some extent and knowing plenty of influential people he found himself here. At a brothel’s bedside mirror and stand staining his lips blood red. And applying plenty of rouge and powder to his eyes and cheeks.

Only for Laszlo would he go undercover in a brothel such as this. It wasn't even the kind he'd frequent. It was filled each night with the craven and depraved denizens of this twisted city. Some so disturbed it even bothered John. Here though, he wasn't John. By day he was Jacob Barnes and by night he was Jezebel Jones, as even a lady boy needed a last name it seemed. 

He was an aging rent boy who as a man had desperately needed shelter. Shelter which the brothel had readily supplied. But everything has its price. His dignity was sacrificed in the agreement. The proprietor had taken one look at Jacob, turned his face to the left and to the right, snapped his fingers, clucked his tongue and gruffly said, “You'll do.” And that was how John became Jacob who became Jezabel at night. 

His age hadn't stopped the customers but thankfully the aphrodisiac laced drug that Laszlo had given him to use worked wonders to put a person to sleep with a smile on their face. Laszlo had guaranteed his safety in that respect. It didn't help John when he was applying the makeup required of him. With the hope that you someone beautiful appeared in the stead of his aging alcoholic self. He too dreaded the thought of anyone he knew seeing him dressed as a strumpet. 

Though when he would gaze in the mirror and see the image of him in lace and ribbons he did feel beautiful, at least when he was finally done with his evening look. As he swept his wigs lengthy locks behind his shoulders and tied it back with a ribbon he hears a knock. One of the servers comes in and speaks softly, “Your client is here, Jacob.” With a smile and slight move towards the boy he pat's the boy's shoulder with one hand and waves him off with the other. 

As the boy moves back to the door, John whispers, “Call me Jezebel and send the gentleman in.” He'd been undercover now for three months and they still hadn't figured out the details that Laszlo needed. He'd report to him each day and after updating his friend, he'd get a small grin and the words, “Perhaps another day Jezebel.” He didn't know much of what his friend needed to find out from this operation. 

John was always told by him, “You'll know it when you see it.” And that was that and John was sent back to the lion's den. With that John would be back at the brothel to become Jezebel once more. Each night to service playboys and perverts. Fluffing his skirts Jezebel strikes a pretty pose to wait for his newest client. As the door opens John breaks character as he whispers, “Teddy.”


	2. 2

John is beside himself in shock. Because all of a sudden it hits him. He's been set up and played by one of his oldest friends. He'd whispered Teddy's name it seemed as Teddy had continued to strip off his outer garments. He'd started with the top coat and was progressing onwards to his shirt and undershirt before John woke from his daze. He moves to stand and address his friend. He loudly says, "Theodore Roosevelt, what on earth?" Theo meets his eyes and that is when John realizes just how far gone his friend is. He's obviously drunken and confused. 

As their eyes meet his friend squints at him and rasps out, "John?" John sees the anger start and knows he must stop it before it worsens. Meeting Teddy in the middle of the room John no Jezebel caresses his friend's face with the palm of his hand and tries to be sultry and whispers, "Ahh my poor Theo." Running his hand down his friend's face to his shoulder and back up to his scalp and rub his fine hair a bit he watches as the rages dies down in his drunken friend's eyes. They're both quiet for a bit but then John speaks, "There is nothing wrong with you Theodore. Don't you dare think so. There is no shame in this my dear Teddy." John can't believe the words nor their impact that they're having on the man in front of him. His shoulders lowered and his head was hanging just a smidge. 

Never one to see such a friend fail and lower himself to these depths John couldn't stand to see such a sight. He uses his hands to life Teddy's chin and have him meet his eyes once more. With that John speaks slowly as to not startle Teddy, "Let's sit and talk a bit my friend." They both seem to purposely avoid the large bed dominating the room and move to sit near his mirror and the door ultimately. Sitting on the small bench by his mirror their knees practically bumping makes John want to laugh a little. But he stifles it as he worries for Theo's reaction to such a thing. 

John figures he should go first, "Laszlo asked this of me, no explanations , just a dire need. But I do fear we've both been had. Tell me Teddy how long have you been doing this to yourself? Laszlo must have known or been informed by one of the working boys. He must have been worried if this is the scheme he dreamed up for us. Tell me Teddy, please just tell me. Be honest, is this why you've been on your lonesome for many years? Myself and even Laszlo have found love, and lost it as well. Just tell me why Theo, please." After all those words spilled out from him John just had to wait in silence as his friend sorted out his thoughts. 

Looking at his friend he quietly realizes what Laszlo must have ages ago, that Teddy wanted to have both. He wanted a masculine man but with a woman's delicate sensibilities. And it seemed that when John had finally accepted the oddity of the assignment that he fit the bill of what Teddy was looking for. He chooses to wait, let the quiet linger until Teddy speaks, "It's always there, this perverted and shameful want, this need to have this, this..." He's quiet once more as John seeks to understand. John as Jezabel had had his eyes opened to this part of society’s underworld. It hadn’t ever really been a particular interest of his before, but now for some reason he found himself enjoying parts of it. 

Grasping Theo’s hands in his, trying to get the man to unclench his fists while they sat quietly on the bench. John knowing it was now his turn to try and aide Teddy in the only way he now could. Barely at a whisper he asks Teddy, “ Well would you like that with me? Because being Jezabel had allowed me to find something out of myself as well.” He knows he’s blushing as he refuses to look at Teddy and speak too. He finds himself surprised as Teddy moves his hands away and begins to caress his shoulder and as they both sit there his friend replies, “Well you do look beautiful tonight.” John knows what started as a simple blush had become a fiery red even in the dim club lighting. 

He knows he should clear the air a bit though, “Only for you Theo. I’ve used Laszlo’s medicines to be but a tease for the others. But for you, I can be this beautiful. If that is what you truly want.” He doesn’t particularly want to carry out the charade that was Jezebel Jones. But for this man he would. He’s pleased as Teddy gruffly replies, “ No, no you’re mine. Not like this, no matter what you look like, this is not what I truly want, change those clothes and let us leave this blasted place.” Both of them move to stand and while Teddy looks determined not to think of the situation they find themselves in John knows he should still do so. 

With a practiced sashay across the room to the cupboard of borrowed dresses and see through gowns John knows what he wants. He speaks as he looks through the gowns absentmindedly, “Theo, you may stay as I change. After all you’ve already seen me as Jezabel.” As Jacob he’d fully embraced living and working as a lady. However sinful that lady may have been. However his wardrobe was mostly too sultry to be worn on the downtown streets. He did however have one dress he had actually bought with the allowance Laszlo had given him for the duration of this mission. He had adored the look of it on the mannequin as well as on his body when he had tried it on. It was a softened yet sturdy velvet that was done all in shades of emerald green. It fit him well and made his shoulders look stunning. He looked to be a true lady in the dress and for that moment he had felt truly beautiful and not a sham of a creature.

He begins to undue Jezabel’s gown and places it aside once fallen from his body. Leaving the undergarments on as such that they were he steps into his favored dress. As he adjusts it on his body he’s surprised as Teddy comes from behind him to aid him in doing up the back of the dress. He feels the other man’s caress on his shoulders as he does this and seeks to look in the mirror at the both of them. They look right, as if they were meant for this path and not some misplaced miscreants. John fixes his makeup a bit with a powder brush and adjusts his wig a bit. As he is doing so Theo surprises him even more by coming up and hugging his body towards his own and whispers in John’s ear, “ You’re beautiful like this.” He shivers at the words and finishes his look by placing a thick black velvet band with a broach across the apple of his throat. 

Looking once more into the mirror he finds himself pleased with his appearance. Turning he places his hand on Theo’s forearm closest to him and quietly says, “Call me Johanna while we’re like this. He blushes once more as Teddy brings his hand to his lips and says, “What a beautiful name for a beautiful lady.” As they move out of the room to the brothel’s doors he hears a shout or two but it doesn’t matter as John is back and Jacob is gone. And as he had stated Johanna is also back with Jezabel gone as well. He still wanted to shake Laszlo for putting them in this situation especially as he dreaded what was to happen with Teddy sobered up and daylight was upon them. He let those thoughts go as Teddy summoned a carriage for them, he was determined to enjoy what remained of this night. He would speak with Teddy in the day and tell him he had no issues with the pleasures of the flesh that both genders allowed him but that he did expect that his lover would be okay with both aspects of John as well. For now he shared a smile with his unexpected lover and with his assistance got into the waiting carriage to see what this adventure would bring them both.

**Notes for the Chapter:**

> So I actually didn't expect to finish this or even continue it. But nearly 2000 words later you've got another chapter. Thanks for reading this oddity of a fic that came out of the middle of nowhere for me.


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